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The indiscriminate use of herbicides makes weeds resistant, increasing the demand for more efficient herbicides. Novel potential herbicides were prepared from sorbic acid, being 8 dienamides and 6 epoxides. Subsequently, phytotoxic activities of sorbic acid and 14 synthesized compounds were evaluated against sorghum, onion, cucumber, lettuce, and beggartick seeds. Furthermore, the protein target of the most active substance in plants was identified in silico. Among the tested compounds, (2E,4E)-N-(p-fluorophenyl)hexa-2,4-dienamide (2c), (2E,4E)-N -(o-naphthyl) hexa-2,4-dienamide (2d), (E)-N-methylphenyl-3-((2R,3R)-3-methyloxiran-2-yl)acrylamide (3b), (E)-N-bromophenyl-3-((2R,3R)-3-methyloxiran-2-yl)acrylamide (3e), and (E)-N-methoxyphenyl-3-((2R,3R)-3-methyloxiran-2-yl)acrylamide (3f) showed pronounced inhibitory activities, both of shoots and roots, making them candidates for promising herbicides. All compounds altered seed development, and compounds 2c, 2d, 3b, 3e, and 3f presented equal or superior results to the commercial control herbicide S-metolachlor. Docking studies suggest that enzyme mitogen-activated protein kinase can be the target of those compounds. resistant epoxides Subsequently 1 sorghum onion cucumber lettuce seeds Furthermore silico 2E,4ENpfluorophenylhexa2,4dienamide 2E4ENpfluorophenylhexa24dienamide EENpfluorophenylhexadienamide 2E,4E N p fluorophenyl hexa 2,4 dienamide 2E 4E 2 4 E 2c c , (2c) 2E,4EN 2E4EN EEN onaphthyl o naphthyl -(o-naphthyl hexa2,4dienamide hexa24dienamide hexadienamide 2d d (2d) ENmethylphenyl32R,3R3methyloxiran2ylacrylamide ENmethylphenyl32R3R3methyloxiran2ylacrylamide ENmethylphenylRRmethyloxiranylacrylamide methylphenyl 3 2R,3R methyloxiran yl acrylamide 2R 3R R 3b b (3b) ENbromophenyl32R,3R3methyloxiran2ylacrylamide ENbromophenyl32R3R3methyloxiran2ylacrylamide ENbromophenylRRmethyloxiranylacrylamide bromophenyl 3e e (3e) ENmethoxyphenyl32R,3R3methyloxiran2ylacrylamide ENmethoxyphenyl32R3R3methyloxiran2ylacrylamide ENmethoxyphenylRRmethyloxiranylacrylamide methoxyphenyl f (3f roots development Smetolachlor. Smetolachlor S metolachlor. metolachlor S-metolachlor mitogenactivated mitogen activated 4ENpfluorophenylhexa2 4dienamide ENpfluorophenylhexa 2E4E EE 24 2, (2c 4EN EN hexa2 (2d ENmethylphenyl32R 3R3methyloxiran2ylacrylamide ENmethylphenyl ylacrylamide 2R3R RR (3b ENbromophenyl32R ENbromophenyl (3e ENmethoxyphenyl32R ENmethoxyphenyl 4ENpfluorophenylhexa ENmethylphenylR Rmethyloxiranylacrylamide ENbromophenylR ENmethoxyphenylR